The first has good live customer service you can chat with (Jack), but he can't do a .... thing about anything.

You are now the owner, not the customer.  

You need to work with an experienced insurance broker who knows HOAs.  

But there is nothing like real world transactions to learn for real....and to do that you'd need a Broker and you'd take on all of the overhead costs.

Let's compare two scenarios I priced out, Borrower Paid Broker CompensationPurchase Price: $500,000SFR 30 Year Fixed Credit 740 DSCR over 1.00 Meets DTI Requirement 1.

The fact that you’re CREATIVELY thinking about how to position yourself to add value to a transaction as a “broker” or intermediary is an excellent start.  

Good points, I would just insert that most delays nowadays are not the fault of the contractor, but rather the customer who is constantly changing things in the original scope of work.

Mortgage broker.

All three generate leads from insurance claim residents and traveling professionals (medical and the trades).One of the advantages of FF has been that it's forced us to have systems in place to create leases, accept security deposits without co-mingling and provide "live" customer service. 

I've committed myself to being a full-time real estate investor, private money broker and real estate consultant!